Polymeric viscosity modifiers for use in lubricants

Abstract

A lubricating oil composition having greater than 50 wt % of a base oil and 0.1 wt % to 20 wt %, both based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by: A) reacting: a) at least one of a lactone of formula (I) or a derivative thereof: wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms; and  b) at least one compound selected from amines, alcohols and oxazolines; and B) reacting the reaction product of step A) onto an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent. Methods employing the lubricating oil compositions and uses of the lubricating compositions as engine oils are also described.

The invention claimed is: 
     
       1. A lubricating oil composition comprising:
 greater than 50 wt % of a base oil, based on the total weight of the lubricating oil composition, and 
 0.1 wt % to 20 wt %, based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by:
 A) forming a reaction product by reacting components a) and b) in a molar ratio of about 1:1:
 a) at least one of a lactone of formula (I) or a derivative thereof: 
 
 
 
       
         
           
           
               
               
           
         
         
            wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and
 b) at least one compound selected from:
 a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; and 
 a linear, branched cyclic or aromatic alcohol comprising at least one primary or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Forumla (III) and Formula (IV) are as follows: 
 
 
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R 1  is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2  is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1  and R 2  add to a total of 7 to 31 carbon atoms, and 
           
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R 3 , R 4 , and R 5  are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5  add to a total of 7 to 31 carbon atoms; and 
           
           B) reacting the reaction product of step A) onto an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10  alpha-olefins having a number average molecular weight (Mn) of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent. 
         
       
     
     
       2. The lubricating oil composition of  claim 1 , wherein the dispersant viscosity modifier is present in an amount of from about 0.1 wt % to about 10 wt %, based on the total weight of the lubricating oil composition. 
     
     
       3. The lubricating oil composition of  claim 1 , wherein the dispersant viscosity modifier is present in an amount of from about 0.5 wt % to about 8 wt %, based on the total weight of the lubricating oil composition. 
     
     
       4. The lubricating oil composition of  claim 1 , wherein the dispersant viscosity modifier is present in an amount of 1 wt % to about 5 wt %, based on the total weight of the lubricating oil composition. 
     
     
       5. The lubricating oil composition of  claim 1 , wherein the base oil is selected from a Group II base oil having at least 90 wt % saturates, a Group III base oil having at least 90 wt % saturates, a Group IV base oil, a Group V base oil and mixtures of two or more thereof. 
     
     
       6. The lubricating oil composition of  claim 1 , wherein the copolymer is an ethylene-propylene copolymer. 
     
     
       7. The lubricating oil composition of  claim 1 , wherein the copolymer is acylated with an ethylenically unsaturated acylating agent having at least one carboxylic acid or carboxylic anhydride group. 
     
     
       8. The lubricating oil composition of  claim 7 , wherein the acylating agent is maleic anhydride. 
     
     
       9. The lubricating oil composition of  claim 1 , wherein component b) is an N-arylphenylene diamine of the formula II: 
       
         
           
           
               
               
           
         
       
       wherein R 1  is hydrogen, —NH-aryl, —NH-arylalkyl, —NH-alkyl or a branched or straight chain radical having from 4 to 24 carbon atoms selected from an alkyl group, an alkenyl group, an alkoxyl group, an aralkyl group, an alkaryl group, a hydroxyalkyl group and an aminoalkyl group; R 2  is —NH 2 , CH 2 —(CH 2 ) n —NH 2 , or CH 2 -aryl-NH 2 , in which n has a value from 1 to 10; and R 3  is selected from a hydrogen, an alkyl group, an alkenyl group, an alkoxyl group, an aralkyl group, and an alkaryl group having from 4 to 24 carbon atoms. 
     
     
       10. The lubricating oil composition of  claim 9 , wherein component b) is selected from the group consisting of 1-(2-amino-ethyl)imidazolidin-2-one, 4-(3-aminopropyl) morpholine, 3-(dimethylamino)-1-propylamine, N-phenyl-p-phenylenedi amine, N-(3-aminopropyl)-2-pyrrolidinone, aminoethyl-acetamide, β-alanine methyl ester, 1-(3-aminopropyl)imidazole, branched β-amines, arylamines, polyetheramines, and poly(arylamines). 
     
     
       11. The lubricating oil composition of  claim 9 , wherein component b) is selected from the group consisting of N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, and N-phenyl-1,2-phenylenediamine. 
     
     
       12. The lubricating oil composition of  claim 9 , wherein the amine is N-phenyl-1,4-phenylenediamine. 
     
     
       13. The lubricating oil composition of  claim 1 , wherein in step A) the lactone is employed and the lactone is selected from acetolactone, propiolactone, butyrolactone, valerolactone, caprolactone, δ-valerolactone, methyl-δ-valero-lactone, ε-caprolactone, methyl-ε-caprolactone, dimethyl-ε-caprolactone, methoxy-ε-caprolactone, cyclohexyl-ε-caprolactone, methylbenzyl-ε-caprolactone, caprylolactone, and methyl-caprylolactone. 
     
     
       14. The lubricating oil composition of  claim 1 , wherein the lactone is c-caprolactone. 
     
     
       15. The lubricating oil composition of  claim 1 , wherein the composition further comprises one or more of antioxidants, friction modifiers, anti-wear agents, detergents, antifoam agents, process oil, and dispersants. 
     
     
       16. The lubricating oil composition of  claim 1 , wherein the dispersant viscosity modifier is further reacted with a component c), wherein component c) is at least one compound selected from:
 a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and an oxazoline. 
 
     
     
       17. The lubricating oil composition of  claim 16 , wherein component c) is selected from, N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, N-phenyl-1,2-phenylenediamine, and dioctyl amine. 
     
     
       18. The lubricating oil composition of  claim 16 , wherein component c) is selected from the group consisting of 2-ethylhexanol, 2-butyloctanol, isomyristyl alcohol, 2-hexyldecanol, isostearyl alcohol, 2-octyldodecanol, 2-decyltetradecanol, 2-dodecylhexadecanol, 2-tetradecyloctadecanol 2-dodecylhexadecanol, 2-hexyloctanol 2-ethylhexanol, 2-hydroxy-2,3-dimethylhexane, 2-butylhexanol, 2-propylhexan-1-ol, 3-Propyl-1-hexanol, 3-methyl-1-heptanol, 3-ethylheptan-1-ol, 2-ethyl-4-methylhexan-1-ol, 2,4-diethylhexan-1-ol, 2-naphthol, benzyl alcohol, 3-phenoxybenzyl alcohol, 2-naphthylmethanol, 9-anthracenemethanol, 1-pyrenemethanol, 2-(9-anthracenylmethoxy)ethanol, 2-(9-anthracenyloxyethanol), and 1-naphthalene methanol. 
     
     
       19. The lubricating oil composition of  claim 16 , wherein component c) is 2-phenyl-2-oxazoline; 2-ethyl-2 oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2 oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2-(2,6-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-[1-(hydroxymethyl)ethyl] oxazoline; mixtures thereof, and derivatives thereof. In yet other approaches, the oxazoline or derivative thereof includes pendant groups in positions 2, 4, and 5 or combinations thereof wherein the pendant groups are selected from heterocyclic, aromatics, hydrocarbyl groups of C 1  to C 32 , and mixtures thereof. 
     
     
       20. A method of improving the soot or sludge handling capability of an engine oil, comprising a step of lubricating an engine with the lubricating oil composition as claimed in  claim 1 . 
     
     
       21. The method of  claim 20 , wherein the improvement in soot or sludge handling is measured relative to a same lubricating oil composition that does not contain the dispersant viscosity modifier. 
     
     
       22. A method of improving thin film and boundary layer friction in an engine comprising the step of lubricating the engine with the lubricating oil composition as claimed in  claim 1 . 
     
     
       23. The method as claimed in  claim 22 , wherein the improved thin film and boundary layer friction is determined relative to a same composition that does not contain the dispersant viscosity modifier. 
     
     
       24. A method for improving boundary layer friction in an engine, comprising the step of lubricating the engine with the lubricating oil composition as claimed in  claim 1 . 
     
     
       25. The method as claimed in  claim 24 , wherein the improved boundary layer friction is determined relative to a same composition that does not contain the dispersant viscosity modifier. 
     
     
       26. A method for improving thin film friction in an engine, comprising the step of lubricating the engine with the lubricating oil composition as claimed in  claim 1 . 
     
     
       27. The method as claimed in  claim 26 , wherein the improved thin film friction is determined relative to a same composition in the absence of the dispersant viscosity modifier. 
     
     
       28. A process for making a polymeric composition comprising the steps of:
 A) forming a reaction product by reacting components a) and b) in a molar ratio of about 1:1:
 a) a lactone of formula (I) or a derivative thereof: 
 
 
       
         
           
           
               
               
           
         
          wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and
 b) at least one compound selected from: 
 a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; 
 a linear, branched cyclic or aromatic alcohol comprising at least one primary, or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Formula (III) and Formula (IV) are as follows: 
 
       
       
         
           
           
               
               
           
         
         
           
             wherein R 1  is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2  is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1  and R 2  add to a total of 7 to 31 carbon atoms, and 
           
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R 3 , R 4 , and R 5  are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5  add to a total of 7 to 31 carbon atoms; and 
           
         
         B) reacting the reaction product of step A) to an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10  alpha-olefins having a number average molecular weight Mn of 5,000 to 200,000 g/mol as measured by GPC. 
       
     
     
       29. The method of  claim 28 , wherein the acylated olefin copolymer is reacted with a component c) prior to reacting with the reaction product of step A), wherein component c) is at least one compound selected from:
 a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; 
 a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and 
 an oxazoline. 
 
     
     
       30. The method of  claim 28 , wherein step B) is carried out at a temperature range of from 115° C. to 250° C. 
     
     
       31. The method of  claim 29 , wherein the reaction of the acylated olefin copolymer and component c) is carried out at a temperature of from 115° C. to 250° C. for 1 to 5 hours and step B) is carried out at a temperature of from 115° C. to 250° C. 
     
     
       32. A lubricating oil composition comprising:
 greater than 50 wt % of a base oil, based on the total weight of the lubricating oil composition, and 
 0.1 wt % to 20 wt %, based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by:
 A) forming a first reaction product by reacting components a) and b) in a molar ratio of about 1:1:
 a) at least one of a lactone of formula (I) or a derivative thereof: 
 
 
 
       
         
           
           
               
               
           
         
         
           
             wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and 
             b) at least one compound selected from: 
             a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; 
             a linear, branched cyclic or aromatic alcohol comprising at least one primary or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Formula (III) and Formula (IV) are as follows: 
           
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R 1  is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2  is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1  and R 2  add to a total of 7 to 31 carbon atoms, and 
           
         
       
       
         
           
           
               
               
           
         
         
           
             wherein R 3 , R 4 , and R 5  are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5  add to a total of 7 to 31 carbon atoms; and 
           
           B) forming a second reaction product by reacting:
 c) at least one compound selected from: 
 
           a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group;
 a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and 
 an oxazoline; and 
 d) an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10  alpha-olefins having a number average molecular weight (Mn) of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent; 
 
           C) reacting the first and the second reaction product of steps A) and B). 
         
       
     
     
       33. The lubricating oil composition of  claim 32 , wherein component b) is an amine, and component c) is an amine. 
     
     
       34. The lubricating oil composition of  claim 33 , wherein the amine of components b) and c) is N-phenyl-1,4-phenylenediamine.